Structure

Physi-Chem Properties

Molecular Weight:  626.56
Volume:  710.15
LogP:  9.882
LogD:  5.171
LogS:  -7.65
# Rotatable Bonds:  22
TPSA:  68.4
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.078
Synthetic Accessibility Score:  4.858
Fsp3:  0.875
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.804
MDCK Permeability:  1.815192081267014e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.966
20% Bioavailability (F20%):  0.978
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  94.18518829345703%
Volume Distribution (VD):  0.661
Pgp-substrate:  4.4611663818359375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.539
CYP2C19-inhibitor:  0.061
CYP2C19-substrate:  0.042
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.025
CYP2D6-inhibitor:  0.994
CYP2D6-substrate:  0.91
CYP3A4-inhibitor:  0.024
CYP3A4-substrate:  0.056

ADMET: Excretion

Clearance (CL):  2.877
Half-life (T1/2):  0.023

ADMET: Toxicity

hERG Blockers:  0.962
Human Hepatotoxicity (H-HT):  0.985
Drug-inuced Liver Injury (DILI):  0.067
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.978
Carcinogencity:  0.01
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.743

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC78375

Natural Product ID:  NPC78375
Common Name*:   Isoprosopilosidine
IUPAC Name:   (2R,3R,6S)-6-[10-[8-[10-[(2R,5R,6S)-5-hydroxy-6-methylpiperidin-2-yl]decyl]-2,3-dihydro-1H-indolizin-4-ium-6-yl]decyl]-2-methylpiperidin-3-ol
Synonyms:   Isoprosopilosidine
Standard InCHIKey:  ZSATVXRUAGIIJL-NMHXFYNSSA-N
Standard InCHI:  InChI=1S/C40H72N3O2/c1-32-39(44)27-25-36(41-32)22-17-13-9-5-3-7-11-15-20-34-30-35(38-24-19-29-43(38)31-34)21-16-12-8-4-6-10-14-18-23-37-26-28-40(45)33(2)42-37/h30-33,36-37,39-42,44-45H,3-29H2,1-2H3/q+1/t32-,33+,36+,37-,39-,40-/m1/s1
SMILES:  C[C@H]1N[C@@H](CCCCCCCCCCc2cc(CCCCCCCCCC[C@@H]3CC[C@H]([C@@H](N3)C)O)c3[n+](c2)CCC3)CC[C@H]1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL541962
PubChem CID:   44157065
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO24830.1 Prosopis glandulosa Under-species n.a. n.a. n.a. n.a. n.a. PMID[19105653]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 4.5 ug.mL-1 PMID[464256]
NPT457 Cell Line BT-549 Homo sapiens IC50 = 6.75 ug.mL-1 PMID[464256]
NPT91 Cell Line KB Homo sapiens IC50 = 7.0 ug.mL-1 PMID[464256]
NPT916 Cell Line SK-MEL Homo sapiens IC50 = 3.3 ug.mL-1 PMID[464256]
NPT857 Cell Line LLC-PK1 Sus scrofa IC50 = 21.3 ug.mL-1 PMID[464256]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 > 23.8 ug.mL-1 PMID[464256]
NPT633 Organism Leishmania donovani Leishmania donovani IC90 = 2.5 ug.mL-1 PMID[464256]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 0.8 ug.mL-1 PMID[464256]
NPT2 Others Unspecified Ratio IC50 > 198.0 n.a. PMID[464256]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.12 ug.mL-1 PMID[464256]
NPT2 Others Unspecified Ratio IC50 > 567.0 n.a. PMID[464256]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.042 ug.mL-1 PMID[464256]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MFC = 10.0 ug ml-1 PMID[464256]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 10.0 ug.mL-1 PMID[464256]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus IC50 = 6.5 ug.mL-1 PMID[464256]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare MIC = 2.5 ug.mL-1 PMID[464256]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare IC50 = 1.5 ug.mL-1 PMID[464256]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 20.0 ug ml-1 PMID[464256]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1.25 ug.mL-1 PMID[464256]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 0.6 ug.mL-1 PMID[464256]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MFC = 1.25 ug ml-1 PMID[464256]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 1.25 ug.mL-1 PMID[464256]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 0.55 ug.mL-1 PMID[464256]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC78375 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC476446
1.0 High Similarity NPC469813
0.8061 Intermediate Similarity NPC311276
0.8037 Intermediate Similarity NPC469762
0.8 Intermediate Similarity NPC150048
0.8 Intermediate Similarity NPC203754
0.7975 Intermediate Similarity NPC469785
0.7952 Intermediate Similarity NPC40779
0.7914 Intermediate Similarity NPC80597
0.7914 Intermediate Similarity NPC212376
0.7914 Intermediate Similarity NPC75540
0.7914 Intermediate Similarity NPC211572
0.7914 Intermediate Similarity NPC70922
0.7907 Intermediate Similarity NPC133261
0.7874 Intermediate Similarity NPC472110
0.7874 Intermediate Similarity NPC472109
0.7853 Intermediate Similarity NPC25008
0.7853 Intermediate Similarity NPC469786
0.7853 Intermediate Similarity NPC469760
0.7853 Intermediate Similarity NPC469763
0.7853 Intermediate Similarity NPC73952
0.7853 Intermediate Similarity NPC469765
0.7853 Intermediate Similarity NPC259644
0.7751 Intermediate Similarity NPC49954
0.7751 Intermediate Similarity NPC54988
0.7751 Intermediate Similarity NPC160105
0.7751 Intermediate Similarity NPC474561
0.7738 Intermediate Similarity NPC194640
0.7714 Intermediate Similarity NPC233936
0.7709 Intermediate Similarity NPC95783
0.7706 Intermediate Similarity NPC201700
0.7706 Intermediate Similarity NPC63751
0.7679 Intermediate Similarity NPC282231
0.7674 Intermediate Similarity NPC472123
0.7674 Intermediate Similarity NPC314603
0.7657 Intermediate Similarity NPC300688
0.7644 Intermediate Similarity NPC151939
0.7619 Intermediate Similarity NPC279918
0.7609 Intermediate Similarity NPC265576
0.7605 Intermediate Similarity NPC129721
0.7602 Intermediate Similarity NPC317430
0.7586 Intermediate Similarity NPC472122
0.7586 Intermediate Similarity NPC24594
0.7582 Intermediate Similarity NPC471313
0.7582 Intermediate Similarity NPC471311
0.7574 Intermediate Similarity NPC71079
0.7571 Intermediate Similarity NPC472108
0.7571 Intermediate Similarity NPC139291
0.756 Intermediate Similarity NPC230869
0.7557 Intermediate Similarity NPC187827
0.7557 Intermediate Similarity NPC472105
0.7543 Intermediate Similarity NPC68354
0.7543 Intermediate Similarity NPC326575
0.7542 Intermediate Similarity NPC474707
0.7529 Intermediate Similarity NPC474217
0.7515 Intermediate Similarity NPC255229
0.7515 Intermediate Similarity NPC81229
0.75 Intermediate Similarity NPC324611
0.7486 Intermediate Similarity NPC62510
0.7486 Intermediate Similarity NPC474177
0.7485 Intermediate Similarity NPC314372
0.7472 Intermediate Similarity NPC163055
0.7459 Intermediate Similarity NPC65215
0.7459 Intermediate Similarity NPC173028
0.7451 Intermediate Similarity NPC166424
0.7451 Intermediate Similarity NPC245244
0.7451 Intermediate Similarity NPC146373
0.7444 Intermediate Similarity NPC94752
0.7443 Intermediate Similarity NPC59269
0.7442 Intermediate Similarity NPC127730
0.7442 Intermediate Similarity NPC278366
0.7436 Intermediate Similarity NPC69914
0.7429 Intermediate Similarity NPC329688
0.7429 Intermediate Similarity NPC189812
0.7429 Intermediate Similarity NPC275305
0.7429 Intermediate Similarity NPC37423
0.7427 Intermediate Similarity NPC102423
0.7421 Intermediate Similarity NPC475288
0.7419 Intermediate Similarity NPC89490
0.741 Intermediate Similarity NPC105818
0.741 Intermediate Similarity NPC24678
0.7403 Intermediate Similarity NPC204565
0.7403 Intermediate Similarity NPC317030
0.7396 Intermediate Similarity NPC193740
0.7396 Intermediate Similarity NPC167635
0.7394 Intermediate Similarity NPC475506
0.7389 Intermediate Similarity NPC256893
0.7386 Intermediate Similarity NPC27740
0.7384 Intermediate Similarity NPC85918
0.738 Intermediate Similarity NPC100321
0.7372 Intermediate Similarity NPC476131
0.7372 Intermediate Similarity NPC329896
0.7372 Intermediate Similarity NPC475105
0.7372 Intermediate Similarity NPC475090
0.7371 Intermediate Similarity NPC313791
0.7368 Intermediate Similarity NPC329825
0.7365 Intermediate Similarity NPC470233
0.7362 Intermediate Similarity NPC190296
0.7354 Intermediate Similarity NPC155143
0.7354 Intermediate Similarity NPC476874
0.7351 Intermediate Similarity NPC133366
0.7345 Intermediate Similarity NPC248454
0.733 Intermediate Similarity NPC469938
0.7326 Intermediate Similarity NPC473640
0.7314 Intermediate Similarity NPC470498
0.731 Intermediate Similarity NPC131718
0.7303 Intermediate Similarity NPC141377
0.7303 Intermediate Similarity NPC176199
0.7303 Intermediate Similarity NPC215795
0.7301 Intermediate Similarity NPC469766
0.7293 Intermediate Similarity NPC15102
0.7283 Intermediate Similarity NPC473763
0.7283 Intermediate Similarity NPC117244
0.7278 Intermediate Similarity NPC48938
0.7273 Intermediate Similarity NPC477976
0.7273 Intermediate Similarity NPC281049
0.7273 Intermediate Similarity NPC476322
0.7268 Intermediate Similarity NPC213629
0.7263 Intermediate Similarity NPC193761
0.7263 Intermediate Similarity NPC15840
0.7257 Intermediate Similarity NPC194411
0.7254 Intermediate Similarity NPC314957
0.7239 Intermediate Similarity NPC469779
0.7239 Intermediate Similarity NPC469768
0.7239 Intermediate Similarity NPC469767
0.7239 Intermediate Similarity NPC469780
0.7239 Intermediate Similarity NPC469784
0.7239 Intermediate Similarity NPC469761
0.7239 Intermediate Similarity NPC469783
0.7238 Intermediate Similarity NPC165495
0.7238 Intermediate Similarity NPC228835
0.7232 Intermediate Similarity NPC472586
0.7228 Intermediate Similarity NPC469501
0.7228 Intermediate Similarity NPC469470
0.7228 Intermediate Similarity NPC3715
0.7225 Intermediate Similarity NPC98715
0.7216 Intermediate Similarity NPC158129
0.7216 Intermediate Similarity NPC162860
0.7211 Intermediate Similarity NPC300183
0.7207 Intermediate Similarity NPC126709
0.7207 Intermediate Similarity NPC248041
0.7202 Intermediate Similarity NPC40070
0.7202 Intermediate Similarity NPC323927
0.7202 Intermediate Similarity NPC166492
0.7202 Intermediate Similarity NPC473362
0.7198 Intermediate Similarity NPC163421
0.7198 Intermediate Similarity NPC188387
0.7191 Intermediate Similarity NPC267885
0.719 Intermediate Similarity NPC265605
0.719 Intermediate Similarity NPC48564
0.719 Intermediate Similarity NPC182570
0.7188 Intermediate Similarity NPC329708
0.7188 Intermediate Similarity NPC165349
0.7188 Intermediate Similarity NPC118832
0.7188 Intermediate Similarity NPC47059
0.7188 Intermediate Similarity NPC264166
0.7188 Intermediate Similarity NPC274291
0.7184 Intermediate Similarity NPC470508
0.7184 Intermediate Similarity NPC477975
0.7182 Intermediate Similarity NPC469358
0.7182 Intermediate Similarity NPC19679
0.7181 Intermediate Similarity NPC229332
0.7178 Intermediate Similarity NPC73767
0.7175 Intermediate Similarity NPC34508
0.717 Intermediate Similarity NPC471322
0.7169 Intermediate Similarity NPC159856
0.7168 Intermediate Similarity NPC59779
0.7168 Intermediate Similarity NPC124542
0.7168 Intermediate Similarity NPC471177
0.7166 Intermediate Similarity NPC195239
0.7166 Intermediate Similarity NPC157828
0.716 Intermediate Similarity NPC471312
0.7158 Intermediate Similarity NPC470497
0.7158 Intermediate Similarity NPC478077
0.7158 Intermediate Similarity NPC235684
0.7157 Intermediate Similarity NPC476492
0.7151 Intermediate Similarity NPC145885
0.7151 Intermediate Similarity NPC84827
0.7151 Intermediate Similarity NPC14113
0.7151 Intermediate Similarity NPC56765
0.7143 Intermediate Similarity NPC472294
0.7143 Intermediate Similarity NPC320968
0.7135 Intermediate Similarity NPC149155
0.7135 Intermediate Similarity NPC285469
0.7135 Intermediate Similarity NPC110500
0.7135 Intermediate Similarity NPC203468
0.7128 Intermediate Similarity NPC11445
0.7128 Intermediate Similarity NPC223791
0.7128 Intermediate Similarity NPC478158
0.7128 Intermediate Similarity NPC107077
0.7127 Intermediate Similarity NPC71037
0.7113 Intermediate Similarity NPC225821
0.7113 Intermediate Similarity NPC54420
0.7113 Intermediate Similarity NPC46225
0.7111 Intermediate Similarity NPC11126
0.7111 Intermediate Similarity NPC213468
0.7111 Intermediate Similarity NPC283219
0.7111 Intermediate Similarity NPC248462
0.711 Intermediate Similarity NPC322976
0.711 Intermediate Similarity NPC324203

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC78375 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7988 Intermediate Similarity NPD5255 Approved
0.7937 Intermediate Similarity NPD4702 Approved
0.7937 Intermediate Similarity NPD4703 Approved
0.7911 Intermediate Similarity NPD3717 Discontinued
0.7816 Intermediate Similarity NPD8408 Discontinued
0.7746 Intermediate Similarity NPD8122 Approved
0.7746 Intermediate Similarity NPD8123 Approved
0.7679 Intermediate Similarity NPD8026 Phase 1
0.763 Intermediate Similarity NPD5065 Approved
0.7602 Intermediate Similarity NPD5862 Discovery
0.76 Intermediate Similarity NPD4079 Approved
0.76 Intermediate Similarity NPD4076 Approved
0.7558 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD6595 Phase 3
0.7556 Intermediate Similarity NPD6068 Discontinued
0.7546 Intermediate Similarity NPD7469 Discontinued
0.7543 Intermediate Similarity NPD3506 Approved
0.7543 Intermediate Similarity NPD2144 Approved
0.7543 Intermediate Similarity NPD3505 Approved
0.7514 Intermediate Similarity NPD8063 Discontinued
0.75 Intermediate Similarity NPD4640 Approved
0.75 Intermediate Similarity NPD8021 Approved
0.75 Intermediate Similarity NPD4639 Approved
0.75 Intermediate Similarity NPD8020 Approved
0.75 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4638 Approved
0.75 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD3082 Discontinued
0.7486 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD2380 Approved
0.7486 Intermediate Similarity NPD2382 Approved
0.7486 Intermediate Similarity NPD2381 Approved
0.7474 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD3475 Approved
0.7436 Intermediate Similarity NPD3476 Approved
0.7429 Intermediate Similarity NPD5322 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD8129 Discovery
0.7416 Intermediate Similarity NPD3038 Discontinued
0.7414 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD8431 Approved
0.7396 Intermediate Similarity NPD2581 Approved
0.7396 Intermediate Similarity NPD2582 Approved
0.7389 Intermediate Similarity NPD5555 Phase 1
0.7386 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD750 Phase 2
0.7355 Intermediate Similarity NPD991 Phase 2
0.7355 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD7944 Discontinued
0.7345 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD6026 Approved
0.733 Intermediate Similarity NPD2928 Phase 2
0.7323 Intermediate Similarity NPD4555 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD3117 Approved
0.7314 Intermediate Similarity NPD3116 Approved
0.7299 Intermediate Similarity NPD5021 Discontinued
0.7296 Intermediate Similarity NPD3944 Approved
0.7296 Intermediate Similarity NPD3942 Approved
0.7277 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD1427 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2118 Approved
0.7244 Intermediate Similarity NPD2119 Approved
0.7222 Intermediate Similarity NPD1380 Discovery
0.7219 Intermediate Similarity NPD2837 Discontinued
0.7211 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD1722 Approved
0.7193 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD268 Approved
0.719 Intermediate Similarity NPD271 Approved
0.7189 Intermediate Similarity NPD4699 Discontinued
0.7188 Intermediate Similarity NPD4122 Approved
0.7188 Intermediate Similarity NPD32 Approved
0.7188 Intermediate Similarity NPD8169 Discontinued
0.7188 Intermediate Similarity NPD31 Approved
0.7188 Intermediate Similarity NPD4034 Approved
0.7188 Intermediate Similarity NPD4039 Approved
0.7188 Intermediate Similarity NPD4036 Approved
0.7188 Intermediate Similarity NPD4033 Approved
0.7188 Intermediate Similarity NPD4035 Approved
0.7188 Intermediate Similarity NPD4038 Approved
0.7188 Intermediate Similarity NPD4037 Approved
0.7186 Intermediate Similarity NPD4547 Phase 3
0.7182 Intermediate Similarity NPD5596 Phase 2
0.7182 Intermediate Similarity NPD2092 Phase 2
0.7182 Intermediate Similarity NPD2095 Phase 2
0.7182 Intermediate Similarity NPD2094 Phase 2
0.7178 Intermediate Similarity NPD786 Approved
0.7178 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6771 Discontinued
0.7152 Intermediate Similarity NPD3525 Discontinued
0.7152 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD7957 Phase 1
0.7143 Intermediate Similarity NPD2096 Phase 2
0.7143 Intermediate Similarity NPD2091 Phase 2
0.7143 Intermediate Similarity NPD748 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD482 Approved
0.7126 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD2896 Discontinued
0.7113 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD4526 Approved
0.7112 Intermediate Similarity NPD4528 Approved
0.7112 Intermediate Similarity NPD4529 Approved
0.711 Intermediate Similarity NPD9398 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD2511 Approved
0.7108 Intermediate Similarity NPD3813 Approved
0.7102 Intermediate Similarity NPD7287 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD8272 Phase 2
0.7095 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD4805 Approved
0.7091 Intermediate Similarity NPD1382 Phase 2
0.7091 Intermediate Similarity NPD1383 Phase 3
0.709 Intermediate Similarity NPD7948 Phase 1
0.7083 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD7233 Approved
0.7081 Intermediate Similarity NPD4030 Approved
0.7081 Intermediate Similarity NPD4028 Approved
0.7081 Intermediate Similarity NPD7234 Approved
0.7081 Intermediate Similarity NPD4029 Approved
0.7079 Intermediate Similarity NPD2076 Approved
0.7079 Intermediate Similarity NPD2077 Approved
0.7077 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD9583 Approved
0.7059 Intermediate Similarity NPD4615 Phase 2
0.7056 Intermediate Similarity NPD4181 Approved
0.705 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD6178 Phase 3
0.7048 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD4174 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD6281 Approved
0.7041 Intermediate Similarity NPD3100 Discontinued
0.7039 Intermediate Similarity NPD4736 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD3323 Discontinued
0.7027 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1034 Phase 3
0.7024 Intermediate Similarity NPD8289 Discontinued
0.702 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD8321 Discontinued
0.7 Intermediate Similarity NPD6044 Discontinued
0.6995 Remote Similarity NPD5486 Discontinued
0.6994 Remote Similarity NPD198 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6363 Clinical (unspecified phase)
0.6989 Remote Similarity NPD4550 Clinical (unspecified phase)
0.6989 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6984 Remote Similarity NPD4602 Approved
0.6984 Remote Similarity NPD7618 Phase 3
0.6984 Remote Similarity NPD7619 Phase 3
0.6982 Remote Similarity NPD1661 Suspended
0.6981 Remote Similarity NPD1095 Clinical (unspecified phase)
0.6979 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6978 Remote Similarity NPD8464 Clinical (unspecified phase)
0.6977 Remote Similarity NPD2809 Approved
0.697 Remote Similarity NPD4804 Approved
0.6968 Remote Similarity NPD6569 Phase 2
0.6966 Remote Similarity NPD4024 Phase 3
0.6959 Remote Similarity NPD8072 Approved
0.6957 Remote Similarity NPD4957 Phase 2
0.6954 Remote Similarity NPD2125 Clinical (unspecified phase)
0.6952 Remote Similarity NPD3321 Discontinued
0.6949 Remote Similarity NPD5611 Phase 2
0.6947 Remote Similarity NPD3477 Phase 2
0.6947 Remote Similarity NPD3478 Clinical (unspecified phase)
0.6944 Remote Similarity NPD4128 Approved
0.6943 Remote Similarity NPD9357 Approved
0.6941 Remote Similarity NPD3575 Approved
0.6941 Remote Similarity NPD4374 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3576 Approved
0.694 Remote Similarity NPD3178 Discontinued
0.6939 Remote Similarity NPD8493 Clinical (unspecified phase)
0.6939 Remote Similarity NPD4533 Clinical (unspecified phase)
0.6935 Remote Similarity NPD3330 Phase 1
0.6935 Remote Similarity NPD3002 Clinical (unspecified phase)
0.6935 Remote Similarity NPD3961 Discontinued
0.6932 Remote Similarity NPD6635 Approved
0.6931 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6928 Remote Similarity NPD9396 Approved
0.6928 Remote Similarity NPD1395 Clinical (unspecified phase)
0.6928 Remote Similarity NPD1649 Discontinued
0.6928 Remote Similarity NPD9392 Approved
0.6927 Remote Similarity NPD2123 Phase 3
0.6923 Remote Similarity NPD8386 Phase 2
0.6923 Remote Similarity NPD4683 Phase 3
0.6923 Remote Similarity NPD1683 Approved
0.6919 Remote Similarity NPD3339 Approved
0.6915 Remote Similarity NPD3389 Approved
0.6915 Remote Similarity NPD3393 Approved
0.6915 Remote Similarity NPD3394 Approved
0.691 Remote Similarity NPD6872 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data